


The Regulars

by HardcoreSupernatural



Category: Supernatural
Genre: F/M
Language: English
Status: Completed
Published: 2020-06-23
Updated: 2020-06-23
Packaged: 2021-03-03 20:47:22
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,980
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24881800
Author URL: https://archiveofourown.org/users/HardcoreSupernatural/pseuds/HardcoreSupernatural
Summary: Sam and Dean are regulars at your diner and Dean decides to ask you out.Prompt: “Either ask her out or I will do it for you!”
Relationships: Dean Winchester/You
Comments: 1
Kudos: 30





	The Regulars

**Author's Note:**

> This is a piece for @amanda-teaches 2k Writer + Reader Challenge on Tumblr
> 
> A/N 2: So excited to be part of this challenge! It was so much fun!!!! Hope you all enjoy this cute little fic. I love when Dean gets shy!!! So cute. Please let me know what you think and as always feedback is GOLD!!!!!
> 
> Thank you to @sinful-chihuahua for being a beta!!!
> 
> And thank you to @cloverhighfive, @erins-culinary-service, and @jensengirl83 for helping me think of some ideas for the fic!!! Much appreciated!
> 
> *Also posted on Tumblr: HardcoreSupernatural*

Your hands grip the wheel tightly as your eyes shut and you breathe out slowly. Another day, another shift at the diner that you’ve been employed at for months. It seemed like it never ended but it was your little home-away-from-home. You had to be content with that because without this diner there would be nothing for you.

You got out of the car, messily placing your hair in a bun and pulling out some pieces to frame your face. It was too early in the morning to care about your hair and you knew it would fix itself eventually if you left it alone. You made your way up the small staircase, opening the large metal door of the 50’s themed diner.

As soon as you enter, the smell of fresh bacon and burnt coffee fill your nostrils. You only stop in the back room to place your purse into your locker. You could hear quiet chatter and metal against metal coming from the kitchen and dining area. You pause for a moment, using this time to breathe and letting the silence consume you before your shift.

You were just putting on your white apron when Shurley’s voice echoes through the back kitchen into the breakroom, “Y/N, table 7 is asking for you.”

You pop your head up a bit and meet Shurley’s bright smile, as she continues, “And man, are those boys cute, I could just eat them up, mhm.” You giggle at her amusement and knew exactly who was waiting for you on the other side of the kitchen door.

You grab a pad and pen, placing them both into your apron pocket before walking out the swinging kitchen door into the main dining area, grabbing the coffee pot and two cups and walking over to Table 7.

“Sam...Dean.” You smile at both of them while pouring the black coffee into both cups. The sound of pouring liquid quickly filling the almost empty room.

“Hi, Y/N.” Dean smirks, placing his menu down as his green eyes meet yours. The way he looked in the morning was definitely something; his face was still a little paler than usual, which made his freckle dusted skin stand out more. The bags under his eyes from countless sleepless nights grew heavy yet complemented his face so well and those chapped lips yearning to be touched. Heat starts to rise in your cheeks and you quickly glance away, pulling the pen and pad out of your apron.

“How are my two favorite customers today?” You question, tapping the pen on the pad a couple of times. You smile brightly at both brothers. Seeing them in the morning made your day a whole lot better, they were by far the easiest customers and always told you the most interesting stories about their time on the road.

“Tired,” Sam laughed. “Just got home from a long trip.”

“Where’d you go this time?” The pen and paper was momentarily forgotten as curiosity got the better of you.

“Went to visit some family in Sioux Falls and it was a pretty long week.” Sam explains while setting down his menu.

“Well family can be tough and you boys do seem like you need a fresh, hot meal and some sleep.” You remark, glancing over how beat up they look.

“And don’t forget the pie!” Dean’s ears perk up and a smile tugs across his lips. His smile instantly made you smile, it was contagious. Sam seemed to have noticed the small exchange between you and Dean and he clears his throat.

“I could never.” You tease. “So what can I get you both today?”

“I will get the two eggs combo, scrambled, with sausage and fruit on the side.” Sam said and you jot down his order on your pad before lifting your head and raising an eyebrow at Dean.

“And I will get my usual, sweetheart.” Dean winks.

“Oh Dean you are so full of surprises.” You giggle, making Sam laugh a little in the process. Dean gave him a bitch face and took a sip of his coffee. You like teasing Dean, it was kind of your thing to do. It was like you both played a little game of who can outwit who, you always seemed to win. Or did he just let you?

You write down his order on your pad, and turn around to head back towards the counter. A smile creeps across your face and your hand brings the pen up to your lips once you get to the register, half thinking about the order, half thinking about Dean.

“So who’s that?” Annie asks, lazily wiping the counter down next to you. She rests her head on her hand and continues to wipe with the other. She was your best friend in the diner and you two talked about everything and anything. No surprise that she wanted to know about the two men in your section.

“Oh, Sam and Dean. They come in almost every morning. It’s like they know my schedule or something.” You chuckle, while Annie is side-eyeing the boys, fingertips lightly tapping her face.

“I would kill for men like that to know my schedule.” She responds, finally standing up straight again, her arm spread out on the counter. “So what’s the deal with them?”

“What do you mean?” You pause from what you are doing and look at her. She is completely staring at them, and you are beginning to get embarrassed, and pull her arm a little.

“I mean do you like either of them?” She stares at you, waiting for an answer to which she already knew.

“I don’t know.” You begin to blush, the end of the sentence trailing off a bit.

“Oh my god, you do!” She holds onto your arms. “Tell me, tell me, tell me.” She almost shouts and you place a hand over her mouth to keep her quiet.

“Shh.” You look over to the boys and notice Dean was staring at you; blood starts to rush to your cheeks. “Okay that one.” you whisper.

She looks around your shoulder to see Dean still staring at you, he gives her a slight smile and waves a little.

“Omg, I think he has a thing for you too.” She remarks.

“How could you possibly know that?” She had to be lying right? Dean having a thing for you, no way?

“Oh, he so does.” She starts counting on her fingers, “He comes in here almost everyday, exactly when you are working, he keeps looking over here at you. Come on, this guy likes you, likes you.” She remarks raising her eyebrows, hoping you’d understand that he does. You just couldn’t completely believe it.

You finished putting in their order on the computer and placing their receipt on the line for the cooks, “Annie, you have no idea what you are talking about,” you said, shaking your head in disbelief.

“Come on dude, you totally like her.” Sam tells Dean, shaking his head at how he cannot believe his brother is denying the obvious.

“Yeah right.” he mocks, knowing full well he is lying. Taking another sip of coffee to stop himself from talking.

“Either ask her out or I will do it for you!” Sam says. Dean’s eyes widen from behind the mug and cannot believe what he just heard.

“You wouldn’t.” The mug hits on the table, Dean giving Sam an all too serious face.

“If you don’t by the end of this meal I am going too.” Dean rolls his eyes at his brother's demand and cannot believe he can’t just simply ask you out like any other girl. There was just something about you that stopped him every time. He wanted to treat you differently and he would if he got the chance.

The bell of the kitchen rings pulling you from your conversation with Annie, you straighten your apron a little and grab both plates in each hand. You make your way around the counter and through the dining room to table 7.

“One, scrambled eggs with sausage and fruit for Sam.” You smile placing the plate down in front of him. Him mouthing thanks to you.

“And one, pancake breakfast with hash brown, eggs, and extra bacon for Dean.” You place the food in front of him. His eyes grew wide at the food and he instantly let out a small moan, making you gulp. It was more cute than sexual and you really didn’t know what to do or how to react. You shake your head a bit before finally responding.

“Let me know if you boys need anything else, I will be back shortly.” You patted the table with your hand a few times before turning around to help out other customers and clean up the place.

The boys didn’t seem to need anything and the diner began to start its breakfast rush. You check on them periodically, really only hoping to get a smile out of Dean. Most times he had his mouth full, which makes you laugh. You bring him a piece of apple pie to finish his meal, which he gladly takes and devours within minutes.

You finally pick up their empty plates, top off their coffees and drop the check off.

“Awh, she even drew a cute smiley face on the check,” Dean chuckles, tracing over the face with his finger. And that’s when Sam finally had enough.

“Hey, Y/N,” Sam shouts from across the diner full of people, his voice carrying quite far.

“Sam, no!” Dean groans through his teeth, face buried in embarrassment. You finish pouring a customer’s coffee and make your way over to them. A confused look washing over it.

“Yeah?” You question.

“The food was amazing.” Sam mentions a sigh of relief from Dean.

“That’s good, Sam.” You chuckled a little, mainly confused why he shouted so loud just to tell you the food was great.

“Oh, and um...Dean has something he wants to tell you.” He remarks, sliding out of the booth and heading out the door. Saying bye on his way out. You were now completely lost at this whole interaction and look to Dean for some answers.

You tilted your head at Dean who’s eyes were filled with fear. He slid out of the booth, standing only inches away. Tapping his foot lightly. You could tell he was searching for answers himself for this awkward situation.

“So...what’s up?” You ask, crossing your arms, a reassuring smile on your face.

“Yeah...um...I just wanted to know...if you...want to go to dinner...to dinner with me sometime?” And then it hit you, that he actually did like you. Your face completely blank and his growing again with fear because you weren’t answering him. You didn’t even register the questions fully at first, you never thought in a million years that Dean would like you.

“Are you asking me on a date, Dean?” You tuck a strand of hair behind your ear, smiling slightly.

“Y-yeah.”

“I would love to.” You chime, his face instantly smiling at your reply.

“Awesome!” He beams proudly, “Tomorrow, 7 work?” He questions.

“Sure, you know where I work.” You tease. Meeting his light green eyes again, instantly feeling your heart drop to the ground and butterflies floating in your stomach. You were hooked on him and couldn’t wait for it to be tomorrow.

His hand grabs your arm, fingers curling around the skin in a soft squeeze before dropping down with his fingers lacing with yours. Giving a squeeze and pulling you in to place a gentle kiss on your cheek. Pulling away with a smile, he reaches for his wallet to place a few bills on the table. You watch him leave, hand to your cheek and heart pounding.


End file.
